Hotels near Pleasant Square Ossining

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Top 5 hotels near Pleasant Square at a glance

Windrose On Hudson — 3-star hotel in 3.1 km from Pleasant Square. Guest rating: 8.6/10 — Excellent.
Summer Pool Oasis Custom Bar Arcade Pool Table — 2-star hotel in 0.7 km from Pleasant Square.
Courtyard by Marriott Tarrytown Westchester County — 3-star hotel in 10.9 km from Pleasant Square. Guest rating: 9.0/10 — Wonderful.
SpringHill Suites by Marriott Tarrytown Westchester County — 3-star hotel in 11.2 km from Pleasant Square. Guest rating: 8.8/10 — Excellent.
West Gate Inn Nyack — 3-star hotel in 9.6 km from Pleasant Square. Guest rating: 7.4/10 — Good.

Where to stay near Pleasant Square?

Room, 1 Queen Bed, Mobility Accessible | Desk, laptop workspace, iron/ironing board, cribs (free)

Windrose On Hudson

3.1 km from Pleasant Square

tiffany

$206

$230 total

includes taxes & fees

Aug 31 - Sep 1

Summer Pool Oasis Custom Bar Arcade Pool Table

0.7 km from Pleasant Square

$648

$1,195 total

includes taxes & fees

Sep 1 - Sep 2

Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Brian

$161

$184 total

includes taxes & fees

Sep 20 - Sep 21

Hypo-allergenic bedding available, desk, iron/ironing board

SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

jiayou

$147

$168 total

includes taxes & fees

Sep 3 - Sep 4

West Gate Inn Nyack

9.6 km from Pleasant Square

Edmund

$99

$113 total

includes taxes & fees

Aug 31 - Sep 1

Hilton Garden Inn Westchester Dobbs Ferry, NY

17.7 km from Pleasant Square

Wendy

$130

$149 total

includes taxes & fees

Sep 6 - Sep 7

Room, 2 Queen Beds | In-room safe, desk, cribs (free), rollaway beds (surcharge)

Hilton Pearl River

17.4 km from Pleasant Square

Anrthony

$229

$255 total

includes taxes & fees

Sep 10 - Sep 11

In-room safe, soundproofing, iron/ironing board, WiFi (free)

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

8.5 km from Pleasant Square

Santa

$116

$133 total

includes taxes & fees

Sep 13 - Sep 14

Desk, laptop workspace, blackout drapes, iron/ironing board

Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Christopher

$135

$155 total

includes taxes & fees

Sep 6 - Sep 7

Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

Jiayou

$113

$129 total

includes taxes & fees

Sep 6 - Sep 7

Indoor pool, open 8:30 AM to 9:30 PM, sun loungers

DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Maureen

$122

$142 total

includes taxes & fees

Sep 8 - Sep 9

Westchester Marriott

11.7 km from Pleasant Square

Wilfus

$186

$213 total

includes taxes & fees

Sep 6 - Sep 7

Premium bedding, pillowtop beds, in-room safe, desk

Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

Eric

$125

$171 total

includes taxes & fees

Sep 20 - Sep 21

Budget Motor Inn - Stony Point

12.3 km from Pleasant Square

Kelly

$74

$82 total

includes taxes & fees

Aug 31 - Sep 1

Element by Marriott Spring Valley

14.8 km from Pleasant Square

Deborah

$131

$152 total

includes taxes & fees

Sep 20 - Sep 21

Sheraton Tarrytown Hotel

11.4 km from Pleasant Square

Anne

$167

$191 total

includes taxes & fees

Sep 6 - Sep 7

Seasonal outdoor pool, open 11:00 AM to 8:00 PM, sun loungers

Daily cooked-to-order breakfast for a fee

Hotel MTK Mount Kisco

13.2 km from Pleasant Square

Alfred

$163

$187 total

includes taxes & fees

Sep 7 - Sep 8

In-room safe, desk, iron/ironing board, cribs (free)

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

14.4 km from Pleasant Square

Yael

$146

$167 total

includes taxes & fees

Sep 7 - Sep 8

Coffee/tea maker, full-size fridge, microwave, stovetop

Hypo-allergenic bedding available, desk, laptop workspace

Sonesta Simply Suites Nanuet

15.1 km from Pleasant Square

BaoTran

$106

$123 total

includes taxes & fees

Sep 20 - Sep 21

Hampton Inn Nanuet

15.1 km from Pleasant Square

Clio

$110

$127 total

includes taxes & fees

Sep 13 - Sep 14

View all properties

Other landmarks near Pleasant Square

Merchants Square

9.0/10 (2 reviews)

If you like spending time outside, why not spend the afternoon at Merchants Square, a park in the heart of Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here? Want to stretch your legs some more? Head to Pleasant Square and Depot Square, both a short walk away.

See properties

Sing Sing Prison Museum

If visiting museums in Ossining are on your list, you might want to check out the upcoming exhibitions at Sing Sing Prison Museum, located in the heart of town. Why not take a stroll along the riverfront and watch the sunset while you're here? If you want to see more of the museums in Ossining, Ossining Historical Society isn't far either.

See properties

Ossining Public Library

If you're planning a bit of sightseeing during your trip, head to Ossining Public Library— just one of the monuments in central Ossining.

See properties

Snowden Avenue Park

Snowden Avenue Park is worth a visit, located 0.3 mi (0.5 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here?

See properties

Depot Square

Depot Square is 0.5 mi (0.8 km) from central Ossining, why not stop by during your stay. Why not take a stroll along the riverfront and watch the sunset while you're here? Want to stretch your legs some more? Head to Louis Engel Waterfront Park and Pleasant Square, both a short walk away.

See properties

Nelson Park

Nelson Park is worth a visit, located 0.7 mi (1.2 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here?

See properties

Crawbuckie Park

Crawbuckie Park is 0.7 mi (1.1 km) from central Ossining, why not stop by during your stay. Want to stretch your legs some more? Head to Croton Point Park and Rockland Lake State Park, both nearby.

See properties

Sing Sing Correctional Facility

Sing Sing Correctional Facility is worth a visit, located 0.7 mi (1.2 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here? It's also full of great shops and restaurants, so you can spend the afternoon having a wander.

See properties